data_global 
_audit_creation_date        "13-09-19"
_audit_creation_method CRYSTALS_ver_14.40

_oxford_structure_analysis_title  'invert in P2(1)'
_chemical_name_systematic         'Leucine-valine co-crystal 0.73:0.27 ratio'
_chemical_melting_point           ?

#looking for refcif 
 
 
# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 
;
222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.14 Ratio
089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.80
220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.35 Ratio
222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.71 Ratio
737_ALERT_1_B D...A   Calc    2.757(3), Rep   2.757(13) ......       4.33 su-Ra
              N12  -O11     1.555   1.545                    #         57
068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
213_ALERT_2_C Atom C34             has ADP max/min Ratio .....       3.30 prola
220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.64 Ratio
234_ALERT_4_C Large Hirshfeld Difference C22    --  C34     ..       0.17 Ang.
242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
245_ALERT_2_C U(iso) H341    Smaller than U(eq) C34     by ...       0.01 AngSq
250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.02
340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          5
737_ALERT_1_C D...A   Calc    3.294(4), Rep   3.294(13) ......       3.25 su-Ra
              C21  -O12     1.555   1.665                    #         57
737_ALERT_1_C D...A   Calc    2.813(4), Rep   2.812(13) ......       3.25 su-Ra
              N12  -O11     1.555   2.546                    #         57
737_ALERT_1_C D...A   Calc    2.876(4), Rep   2.876(13) ......       3.25 su-Ra
              N12  -O22     1.555   1.545                    #         57
737_ALERT_1_C D...A   Calc    3.351(4), Rep   3.351(13) ......       3.25 su-Ra
              N11  -C12     1.555   1.655                    #         57
737_ALERT_1_C D...A   Calc    3.001(4), Rep   3.001(13) ......       3.25 su-Ra
              N11  -O12     1.555   1.655                    #         57
737_ALERT_1_C D...A   Calc    2.968(4), Rep   2.967(13) ......       3.25 su-Ra
              N11  -O22     1.555   1.655                    #         57
737_ALERT_1_C D...A   Calc    2.747(4), Rep   2.748(13) ......       3.25 su-Ra
              N11  -O12     1.555   2.556                    #         57
737_ALERT_1_C D...A   Calc    2.859(4), Rep   2.859(13) ......       3.25 su-Ra
              N11  -O21     1.555   1.545                    #         57
860_ALERT_3_G Note: Number of Least-Squares Restraints .......        163
301_ALERT_3_G Note: Main Residue  Disorder ...................      36.00 Perc.
432_ALERT_2_G Short Inter X...Y Contact  C51    ..  C54     ..       2.98 Ang.


Due to the disorder present in the structure the values for F000 differ slightly.
The disorder also causes there to be a non-integer number of atoms in the cell.  The 
disorder occupancies add to 100%. There are a number of distance, thermal
and vibrational restraints used to keep the model chemically reasonable. 


910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5
912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         16
913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1


The data are 99.6% complete to the Acta Min resolution.

===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
-------------------------------------------------------------------------------
 20.82     0.500     0.994          830      825        5
 23.01     0.550     0.994         1083     1077        6
 25.24     0.600     0.996         1409     1403        6
------------------------------------------------------------ ACTA Min. Res. ---
 26.67     0.632     0.986         1626     1604       22
 

              
790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C5.73 H12.46 N O2
760_ALERT_1_G CIF Contains no Torsion Angles .................          ?
808_ALERT_5_G No Parsable SHELXL style Weighting Scheme Found           !
811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found          ?

Noted. No action taken.


 
;

data_2
_cell_length_a                    9.5961(6)
_cell_length_b                    5.2810(4)
_cell_length_c                    14.4864(13)
_cell_angle_alpha                 90
_cell_angle_beta                  109.328(5)
_cell_angle_gamma                 90
_cell_volume                      692.75(9)
 
_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'P 1 21 1 ' 
_symmetry_space_group_name_Hall   'P 2yb'
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,y+1/2,-z'

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 N       0.0061   0.0033  12.2126   0.0057   3.1322   9.8933   2.0125  28.9975
   1.1663   0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
_cell_formula_units_Z                    2

# Given Formula = C11 H24 N2 O4 
# Dc =      1.19 Fooo =    276.32 Mu =      0.90 M =    248.32
# Found Formula = C11.27 H24.54 N2 O4 
# Dc =      1.21 FOOO =    276.32 Mu =      0.91 M =    252.11

_chemical_formula_sum             'C11.27 H24.54 N2 O4'
_chemical_formula_moiety          'C5.73 H12.46 N O2, C5.54 H12.08 N O2'
_chemical_compound_source                ?
_chemical_formula_weight            252.11
 
 
_cell_measurement_reflns_used         2433
_cell_measurement_theta_min              4
_cell_measurement_theta_max             27
_cell_measurement_temperature          123
 
_exptl_crystal_description        'plate' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_min           0.120 
_exptl_crystal_size_mid           0.210 
_exptl_crystal_size_max           0.300 
 
_exptl_crystal_density_diffrn     1.209 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              276.320 
_exptl_absorpt_coefficient_mu     0.091 
 
# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_process_details    'SADABS (Siemens, 1996)' 
_exptl_absorpt_correction_T_min   0.79 
_exptl_absorpt_correction_T_max   0.99 
_diffrn_measurement_device_type   'Bruker Kappa Apex2' 
_diffrn_measurement_device        'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method        '\f & \w scans' 
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'Apex2 (Bruker AXS, 2006)' 
_computing_cell_refinement        'Apex2 (Bruker AXS, 2006)' 
_computing_data_reduction         'Apex2 (Bruker AXS, 2006)' 
_computing_structure_solution     'SIR92 (Altomare et al., 1994)' 
_computing_structure_refinement   'CRYSTALS (Betteridge et al., 2003)' 
_computing_publication_material   'CRYSTALS (Betteridge et al., 2003)' 
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)' 
 
_diffrn_standards_interval_time   . 
_diffrn_standards_interval_count  . 
_diffrn_standards_number          0 
_diffrn_standards_decay_%         ? 
 
_diffrn_ambient_temperature        123
_diffrn_reflns_number             5666 
_reflns_number_total              1604 
_diffrn_reflns_av_R_equivalents   0.047 
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1604 
# Theoretical number of reflections is about 2924 
 
 
_diffrn_reflns_theta_min          3.083 
_diffrn_reflns_theta_max          26.670 
_diffrn_measured_fraction_theta_max 0.986 
 
_diffrn_reflns_theta_full         25.070 
_diffrn_measured_fraction_theta_full 0.994 
 
 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        14 
_reflns_limit_h_min               -12 
_reflns_limit_h_max               11 
_reflns_limit_k_min               0 
_reflns_limit_k_max               6 
_reflns_limit_l_min               0 
_reflns_limit_l_max               18 
 
_oxford_diffrn_Wilson_B_factor    2.17 
_oxford_diffrn_Wilson_scale       7.73 
 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    difmap
 
_refine_diff_density_min          -0.23 
_refine_diff_density_max          0.23 
 
 
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
 
 
# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref     I>3.0\s(I)
_refine_ls_number_reflns          1219 
_refine_ls_number_restraints      163 
_refine_ls_number_parameters      210 
_oxford_refine_ls_R_factor_ref    0.0542 
_refine_ls_wR_factor_ref          0.0523 
_refine_ls_goodness_of_fit_ref    1.0346 
_refine_ls_shift/su_max           0.0001517 
_refine_ls_shift/su_mean          0.0000183 
 
 
# The values computed with all filters except I/sigma 
_oxford_reflns_number_all         1603 
_refine_ls_R_factor_all           0.0695 
_refine_ls_wR_factor_all          0.0619 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0\s(I)
_reflns_number_gt                 1270 
_refine_ls_R_factor_gt            0.0561 
_refine_ls_wR_factor_gt           0.0531 
 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  'unk' 
 
 
_refine_ls_structure_factor_coef  F 
_refine_ls_matrix_type            full
_refine_ls_hydrogen_treatment     constr          #undef, noref, refall,
                                                 # refxyz, refU, constr or mixed
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.587 0.604 0.346 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references 
; 
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., 
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. 
 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>, 
Version 2 User Manual, M86-E01078, Madison, WI. 
 
Prince, E. 
Mathematical Techniques in Crystallography 
and Materials Science 
Springer-Verlag, New York, 1982. 
 
Siemens Industrial Automation, Inc (1996). 
SADABS: Area-Detector Absorption Correction;: Madison, WI. 
 
Watkin D.J. (1994). 
Acta Cryst, A50, 411-437. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
; 

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O11 O 0.0983(2) 0.0103(5) 0.40867(17) 0.0256 1.0000 Uani . U . . . . 
C11 C 0.1729(3) 0.1655(7) 0.3786(2) 0.0232 1.0000 Uani . U . . . . 
O21 O 0.1589(2) 0.3998(6) 0.37664(19) 0.0340 1.0000 Uani . U . . . . 
C21 C 0.2875(3) 0.0519(7) 0.3375(3) 0.0297 1.0000 Uani D U . . . . 
N11 N 0.3535(3) -0.1797(6) 0.3938(2) 0.0309 1.0000 Uani . U . . . . 
C31 C 0.2154(4) -0.0230(9) 0.2301(3) 0.0458 1.0000 Uani D U . . . . 
C41 C 0.1744(14) 0.210(2) 0.1658(9) 0.0640 0.540(12) Uani D U P . 1 . 
N12 N -0.1600(2) -0.7944(6) 0.4233(2) 0.0232 1.0000 Uani . U . . . . 
C54 C -0.3680(13) -0.718(3) 0.1974(11) 0.0415 0.270(8) Uani D U P . 4 . 
C22 C -0.2063(3) -0.5706(7) 0.3589(2) 0.0240 1.0000 Uani D U . . . . 
C12 C -0.3383(3) -0.4449(7) 0.3774(2) 0.0210 1.0000 Uani . U . . . . 
O12 O -0.4185(2) -0.5816(6) 0.41018(17) 0.0275 1.0000 Uani . U . . . . 
C42 C 0.1198(17) 0.168(3) 0.1583(13) 0.0940 0.460(12) Uani D . P . 2 . 
C61 C 0.0752(12) 0.100(3) 0.0676(7) 0.0968 0.540(12) Uani D U P . 1 . 
C51 C 0.3083(13) 0.3431(16) 0.1572(8) 0.0768 0.540(12) Uani D U P . 1 . 
C52 C 0.3122(13) -0.135(4) 0.1767(9) 0.1009 0.460(12) Uani D . P . 2 . 
C43 C -0.3003(5) -0.4773(11) 0.1718(4) 0.0420 0.730(8) Uani D U P . 3 . 
C53 C -0.3567(9) -0.6151(18) 0.0747(5) 0.0760 0.730(8) Uani D U P . 3 . 
C63 C -0.1716(8) -0.3118(14) 0.1724(5) 0.0566 0.730(8) Uani D U P . 3 . 
C33 C -0.2539(6) -0.6773(12) 0.2536(4) 0.0290 0.730(8) Uani D U P . 3 . 
O22 O -0.3602(2) -0.2129(6) 0.35761(18) 0.0317 1.0000 Uani . U . . . . 
C44 C -0.1980(15) -0.350(3) 0.2029(12) 0.0342 0.270(8) Uani D U P . 4 . 
C34 C -0.2206(18) -0.600(3) 0.2508(12) 0.0358 0.270(8) Uani D U P . 4 . 
H211 H 0.3644 0.1771 0.3426 0.0375 1.0000 Uiso R . . . . . 
H411 H 0.1154 0.3258 0.1916 0.0711 0.540(12) Uiso R . P . 1 . 
H541 H -0.3585 -0.8329 0.1486 0.0600 0.270(8) Uiso R . P . 4 . 
H542 H -0.4034 -0.8076 0.2428 0.0601 0.270(8) Uiso R . P . 4 . 
H543 H -0.4370 -0.5871 0.1666 0.0600 0.270(8) Uiso R . P . 4 . 
H421 H 0.0906 0.1084 0.0921 0.1811 0.460(12) Uiso R . P . 2 . 
H423 H 0.1755 0.3220 0.1634 0.1811 0.460(12) Uiso R . P . 2 . 
H422 H 0.0335 0.2012 0.1761 0.1810 0.460(12) Uiso R . P . 2 . 
H612 H 0.0489 0.2326 0.0185 0.1249 0.540(12) Uiso R . P . 1 . 
H611 H 0.1288 -0.0306 0.0469 0.1249 0.540(12) Uiso R . P . 1 . 
H613 H -0.0135 0.0280 0.0750 0.1251 0.540(12) Uiso R . P . 1 . 
H511 H 0.2772 0.4904 0.1152 0.1150 0.540(12) Uiso R . P . 1 . 
H513 H 0.3700 0.3960 0.2223 0.1150 0.540(12) Uiso R . P . 1 . 
H512 H 0.3624 0.2276 0.1297 0.1151 0.540(12) Uiso R . P . 1 . 
H431 H -0.3799 -0.3732 0.1789 0.0531 0.730(8) Uiso R . P . 3 . 
H532 H -0.4137 -0.7586 0.0821 0.1179 0.730(8) Uiso R . P . 3 . 
H531 H -0.2741 -0.6712 0.0567 0.1182 0.730(8) Uiso R . P . 3 . 
H533 H -0.4182 -0.5042 0.0253 0.1182 0.730(8) Uiso R . P . 3 . 
H631 H -0.1334 -0.2298 0.2349 0.0991 0.730(8) Uiso R . P . 3 . 
H633 H -0.0958 -0.4149 0.1619 0.0991 0.730(8) Uiso R . P . 3 . 
H632 H -0.2019 -0.1871 0.1217 0.0989 0.730(8) Uiso R . P . 3 . 
H332 H -0.3340 -0.7936 0.2448 0.0364 0.730(8) Uiso R . P . 3 . 
H331 H -0.1706 -0.7720 0.2469 0.0361 0.730(8) Uiso R . P . 3 . 
H442 H -0.0949 -0.3104 0.2226 0.0671 0.270(8) Uiso R . P . 4 . 
H441 H -0.2492 -0.2181 0.2239 0.0670 0.270(8) Uiso R . P . 4 . 
H443 H -0.2369 -0.3651 0.1332 0.0669 0.270(8) Uiso R . P . 4 . 
H341 H -0.1434 -0.7182 0.2474 0.0251 0.270(8) Uiso R . P . 4 . 
H221 H -0.1244 -0.4497 0.3723 0.0305 1.0000 Uiso R . . . . . 
H312 H 0.2832 -0.1206 0.2099 0.0592 0.540(12) Uiso R . P . 1 . 
H311 H 0.1303 -0.1212 0.2243 0.0592 0.540(12) Uiso R . P . 1 . 
H521 H 0.2564 -0.1773 0.1113 0.1500 0.460(12) Uiso R . P . 2 . 
H522 H 0.3575 -0.2834 0.2104 0.1500 0.460(12) Uiso R . P . 2 . 
H523 H 0.3860 -0.0160 0.1768 0.1500 0.460(12) Uiso R . P . 2 . 
H313 H 0.1493 -0.1585 0.2313 0.0592 0.460(12) Uiso . . P . 2 . 
H121 H -0.0790 -0.8723 0.4108 0.0332 1.0000 Uiso R . . . . . 
H122 H -0.1311 -0.7424 0.4896 0.0332 1.0000 Uiso R . . . . . 
H123 H -0.2390 -0.9114 0.4107 0.0332 1.0000 Uiso R . . . . . 
H111 H 0.4235 -0.2468 0.3670 0.0352 1.0000 Uiso R . . . . . 
H112 H 0.4012 -0.1377 0.4604 0.0352 1.0000 Uiso R . . . . . 
H113 H 0.2791 -0.3018 0.3890 0.0352 1.0000 Uiso R . . . . . 
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0204(9) 0.0149(10) 0.0492(14) 0.0046(9) 0.0220(9) 0.0060(8) 
C11 0.0158(13) 0.0145(10) 0.0437(18) 0.0001(13) 0.0158(12) 0.0022(10) 
O21 0.0341(12) 0.0129(9) 0.0637(17) 0.0008(12) 0.0279(12) 0.0035(9) 
C21 0.0194(12) 0.0209(14) 0.0573(16) -0.0037(12) 0.0243(11) -0.0002(10) 
N11 0.0192(12) 0.0238(14) 0.0552(17) -0.0067(12) 0.0195(12) 0.0061(10) 
C31 0.051(2) 0.046(2) 0.0507(15) 0.0003(15) 0.0304(15) 0.0087(17) 
C41 0.093(6) 0.055(5) 0.059(3) 0.009(3) 0.045(4) 0.032(4) 
N12 0.0157(10) 0.0118(12) 0.0475(15) -0.0019(10) 0.0179(10) 0.0020(8) 
C54 0.030(6) 0.028(6) 0.057(6) -0.006(7) 0.003(5) -0.008(5) 
C22 0.0165(13) 0.0177(13) 0.0429(15) 0.0005(10) 0.0166(12) 0.0021(10) 
C12 0.0140(11) 0.0147(11) 0.0362(17) -0.0051(12) 0.0111(11) 0.0000(9) 
O12 0.0182(9) 0.0200(11) 0.0515(15) -0.0022(10) 0.0212(9) 0.0018(8) 
C42 0.097(11) 0.078(10) 0.069(9) 0.032(8) -0.023(8) -0.034(9) 
C61 0.089(6) 0.148(12) 0.054(4) 0.017(5) 0.025(4) 0.015(6) 
C51 0.136(8) 0.030(4) 0.085(7) 0.001(4) 0.064(6) 0.004(4) 
C52 0.067(7) 0.182(18) 0.068(8) -0.008(10) 0.041(6) 0.029(9) 
C43 0.046(3) 0.038(3) 0.049(2) 0.0111(18) 0.026(2) 0.019(2) 
C53 0.095(5) 0.091(5) 0.042(2) 0.005(3) 0.023(3) -0.004(4) 
C63 0.087(5) 0.031(3) 0.077(5) 0.010(3) 0.062(4) 0.005(3) 
C33 0.032(3) 0.020(3) 0.0439(15) 0.0000(15) 0.0250(19) 0.006(2) 
O22 0.0262(10) 0.0168(9) 0.0586(17) 0.0009(11) 0.0228(11) 0.0046(9) 
C44 0.027(6) 0.030(7) 0.054(7) 0.009(6) 0.025(7) 0.003(5) 
C34 0.024(6) 0.016(7) 0.074(10) -0.005(6) 0.025(6) -0.011(5) 

_refine_ls_extinction_method 
    'None'
_oxford_refine_ls_scale 0.3900(15) 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
O11 . C11 . 1.257(4)    yes
C11 . O21 . 1.244(4)    yes
C11 . C21 . 1.535(3)    yes
C21 . N11 . 1.489(4)    yes
C21 . C31 . 1.532(5)    yes
C21 . H211 . 0.975    no
N11 . H111 . 0.949    no
N11 . H112 . 0.948    no
N11 . H113 . 0.948    no
C31 . C41 . 1.512(12)    yes
C31 . H312 . 0.948    no
C31 . H311 . 0.948    no
C41 . C61 . 1.539(15)    yes
C41 . C51 . 1.507(14)    yes
C41 . H411 . 0.988    no
N12 . C22 . 1.480(4)    yes
N12 . H121 . 0.948    no
N12 . H122 . 0.948    no
N12 . H123 . 0.948    no
C54 . C34 . 1.505(15)    yes
C54 . H541 . 0.959    no
C54 . H542 . 0.959    no
C54 . H543 . 0.959    no
C22 . C12 . 1.531(3)    yes
C22 . C33 . 1.546(7)    yes
C22 . H221 . 0.980    no
C12 . O12 . 1.257(3)    yes
C12 . O22 . 1.259(4)    yes
C42 . H421 . 0.959    no
C42 . H423 . 0.962    no
C42 . H422 . 0.961    no
C61 . H612 . 0.970    no
C61 . H611 . 0.966    no
C61 . H613 . 0.970    no
C51 . H511 . 0.971    no
C51 . H513 . 0.974    no
C51 . H512 . 0.968    no
C52 . H521 . 0.947    no
C52 . H522 . 0.947    no
C52 . H523 . 0.948    no
C43 . C53 . 1.516(9)    yes
C43 . C63 . 1.511(8)    yes
C43 . C33 . 1.540(7)    yes
C43 . H431 . 0.974    no
C53 . H532 . 0.961    no
C53 . H531 . 0.959    no
C53 . H533 . 0.960    no
C63 . H631 . 0.960    no
C63 . H633 . 0.960    no
C63 . H632 . 0.957    no
C33 . H332 . 0.959    no
C33 . H331 . 0.976    no
C44 . C34 . 1.539(18)    yes
C44 . H442 . 0.958    no
C44 . H441 . 0.958    no
C44 . H443 . 0.956    no
C34 . H341 . 0.984    no
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
O11 . C11 . O21 . 125.9(3)    yes
O11 . C11 . C21 . 116.3(3)    yes
O21 . C11 . C21 . 117.8(3)    yes
C11 . C21 . N11 . 109.8(2)    yes
C11 . C21 . C31 . 110.7(2)    yes
N11 . C21 . C31 . 108.1(3)    yes
C11 . C21 . H211 . 109.1    no
N11 . C21 . H211 . 110.0    no
C31 . C21 . H211 . 109.1    no
C21 . N11 . H111 . 108.3    no
C21 . N11 . H112 . 109.9    no
H111 . N11 . H112 . 109.6    no
C21 . N11 . H113 . 110.2    no
H111 . N11 . H113 . 109.6    no
H112 . N11 . H113 . 109.4    no
C21 . C31 . C41 . 110.7(6)    yes
C21 . C31 . H312 . 109.2    no
C41 . C31 . H312 . 108.5    no
C21 . C31 . H311 . 108.5    no
C41 . C31 . H311 . 110.4    no
H312 . C31 . H311 . 109.5    no
C31 . C41 . C61 . 102.7(9)    yes
C31 . C41 . C51 . 112.1(9)    yes
C61 . C41 . C51 . 112.5(9)    yes
C31 . C41 . H411 . 109.7    no
C61 . C41 . H411 . 109.1    no
C51 . C41 . H411 . 110.6    no
C22 . N12 . H121 . 108.7    no
C22 . N12 . H122 . 109.5    no
H121 . N12 . H122 . 109.6    no
C22 . N12 . H123 . 110.2    no
H121 . N12 . H123 . 109.5    no
H122 . N12 . H123 . 109.4    no
C34 . C54 . H541 . 109.8    no
C34 . C54 . H542 . 109.8    no
H541 . C54 . H542 . 109.6    no
C34 . C54 . H543 . 109.0    no
H541 . C54 . H543 . 109.4    no
H542 . C54 . H543 . 109.2    no
N12 . C22 . C12 . 109.2(2)    yes
N12 . C22 . C33 . 105.1(3)    yes
C12 . C22 . C33 . 109.8(3)    yes
N12 . C22 . H221 . 110.0    no
C12 . C22 . H221 . 109.8    no
C33 . C22 . H221 . 112.8    no
C22 . C12 . O12 . 117.5(2)    yes
C22 . C12 . O22 . 117.9(2)    yes
O12 . C12 . O22 . 124.6(2)    yes
C31 . C42 . H421 . 112.1    no
C31 . C42 . H423 . 108.3    no
H421 . C42 . H423 . 109.0    no
C31 . C42 . H422 . 108.4    no
H421 . C42 . H422 . 109.7    no
H423 . C42 . H422 . 109.4    no
C41 . C61 . H612 . 109.7    no
C41 . C61 . H611 . 109.0    no
H612 . C61 . H611 . 108.9    no
C41 . C61 . H613 . 110.0    no
H612 . C61 . H613 . 109.8    no
H611 . C61 . H613 . 109.3    no
C41 . C51 . H511 . 109.4    no
C41 . C51 . H513 . 108.4    no
H511 . C51 . H513 . 109.8    no
C41 . C51 . H512 . 109.1    no
H511 . C51 . H512 . 110.1    no
H513 . C51 . H512 . 110.0    no
C31 . C52 . H521 . 111.2    no
C31 . C52 . H522 . 108.3    no
H521 . C52 . H522 . 109.5    no
C31 . C52 . H523 . 108.9    no
H521 . C52 . H523 . 109.4    no
H522 . C52 . H523 . 109.5    no
C53 . C43 . C63 . 108.9(5)    yes
C53 . C43 . C33 . 108.0(5)    yes
C63 . C43 . C33 . 111.4(5)    yes
C53 . C43 . H431 . 108.5    no
C63 . C43 . H431 . 110.0    no
C33 . C43 . H431 . 110.1    no
C43 . C53 . H532 . 108.4    no
C43 . C53 . H531 . 109.1    no
H532 . C53 . H531 . 109.8    no
C43 . C53 . H533 . 109.9    no
H532 . C53 . H533 . 109.4    no
H531 . C53 . H533 . 110.2    no
C43 . C63 . H631 . 108.8    no
C43 . C63 . H633 . 109.4    no
H631 . C63 . H633 . 109.5    no
C43 . C63 . H632 . 110.7    no
H631 . C63 . H632 . 109.7    no
H633 . C63 . H632 . 108.8    no
C43 . C33 . C22 . 115.2(5)    yes
C43 . C33 . H332 . 108.8    no
C22 . C33 . H332 . 109.1    no
C43 . C33 . H331 . 108.2    no
C22 . C33 . H331 . 107.5    no
H332 . C33 . H331 . 107.8    no
C34 . C44 . H442 . 109.8    no
C34 . C44 . H441 . 108.4    no
H442 . C44 . H441 . 109.5    no
C34 . C44 . H443 . 109.9    no
H442 . C44 . H443 . 109.7    no
H441 . C44 . H443 . 109.5    no
C44 . C34 . C22 . 113.4(12)    yes
C44 . C34 . C54 . 111.9(13)    yes
C22 . C34 . C54 . 108.5(11)    yes
C44 . C34 . H341 . 107.6    no
C22 . C34 . H341 . 107.5    no
C54 . C34 . H341 . 107.7    no
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_site_symmetry_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_site_symmetry_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_A
 _geom_hbond_angle_DHA
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_publ_flag
C21 . H211 . O12 1_665 159.90(10) 0.975 2.361 3.294(13)    yes
C42 . H423 . C51 . 126.4(9) 0.962 1.312 2.036(13)    yes
C61 . H612 . C61 2_555 158.3(5) 0.970 2.399 3.319(13)    yes
C51 . H511 . C52 1_565 120.3(5) 0.971 2.148 2.768(13)    yes
C54 . H332 . N12 . 147.4(11) 0.767 2.572 3.245(13)    yes
C44 . H441 . O22 . 130.5(3) 0.958 2.501 3.207(13)    yes
C63 . H443 . C53 . 153.2(17) 0.748 1.772 2.462(13)    yes
C44 . H443 . C53 . 122.2(5) 0.956 1.772 2.420(13)    yes
C52 . H522 . C51 1_545 125.0(5) 0.947 2.114 2.768(13)    yes
N12 . H121 . O11 1_545 168.70(11) 0.948 1.821 2.757(13)    yes
N12 . H122 . O11 2_546 152.97(10) 0.948 1.935 2.812(13)    yes
N12 . H123 . O22 1_545 158.84(9) 0.948 1.972 2.876(13)    yes
N11 . H111 . C12 1_655 154.02(10) 0.949 2.472 3.351(13)    yes
N11 . H111 . O12 1_655 132.45(9) 0.949 2.278 3.001(13)    yes
N11 . H111 . O22 1_655 146.20(9) 0.949 2.131 2.967(13)    yes
N11 . H112 . O12 2_556 156.99(9) 0.948 1.851 2.748(13)    yes
N11 . H113 . O21 1_545 167.77(9) 0.948 1.926 2.859(13)    yes


_iucr_refine_instruction_details_constraints
;
#
# Punched on 19/09/13 at 16:03:17
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
EQUIV PART (1, OCC) PART (2, OCC) 
WEIGHT -1 PART(2, OCC) 
EQUIV PART (3, OCC) PART (4, OCC) 
WEIGHT -1 PART(4, OCC) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  31,X'S) H   ( 312,X'S) H   ( 311,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) H   ( 543,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 423,X'S) H   ( 422,X'S) 
RIDE C   (  61,X'S) H   ( 612,X'S) H   ( 611,X'S) H   ( 613,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 513,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) H   ( 523,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  53,X'S) H   ( 532,X'S) H   ( 531,X'S) H   ( 533,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) H   ( 633,X'S) H   ( 632,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  44,X'S) H   ( 442,X'S) H   ( 441,X'S) H   ( 443,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints
;
#
# Punched on 19/09/13 at 16:03:17
#
#LIST     16                                                                    
DISTANCE 1.540000 , 0.030000 = C(21) TO C(31) 
DISTANCE 1.510000 , 0.030000 = C(31) TO C(41) 
DISTANCE 1.510000 , 0.030000 = C(41) TO C(51) 
DISTANCE 1.510000 , 0.030000 = C(41) TO C(61) 
DISTANCE 1.510000 , 0.030000 = C(31) TO C(42) 
DISTANCE 1.510000 , 0.030000 = C(31) TO C(52) 
DISTANCE 1.540000 , 0.030000 = C(22) TO C(33) 
DISTANCE 1.540000 , 0.030000 = C(33) TO C(43) 
DISTANCE 1.510000 , 0.030000 = C(43) TO C(53) 
DISTANCE 1.510000 , 0.030000 = C(43) TO C(63) 
DISTANCE 1.540000 , 0.030000 = C(22) TO C(34) 
DISTANCE 1.510000 , 0.030000 = C(34) TO C(44) 
DISTANCE 1.510000 , 0.030000 = C(34) TO C(54) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00100 = O(11) TO C(11) 
VIBR .0, 0.00100 = C(11) TO O(21) 
VIBR .0, 0.00100 = C(11) TO C(21) 
VIBR .0, 0.00300 = O(21) TO O(11) 
VIBR .0, 0.00300 = C(21) TO O(11) 
VIBR .0, 0.00300 = C(21) TO O(21) 
VIBR .0, 0.00100 = C(21) TO N(11) 
VIBR .0, 0.00100 = C(21) TO C(31) 
VIBR .0, 0.00300 = N(11) TO C(11) 
VIBR .0, 0.00300 = C(31) TO C(11) 
VIBR .0, 0.00300 = C(31) TO N(11) 
VIBR .0, 0.00100 = C(31) TO C(41) 
VIBR .0, 0.00300 = C(41) TO C(21) 
VIBR .0, 0.00100 = C(41) TO C(61) 
VIBR .0, 0.00100 = C(41) TO C(51) 
VIBR .0, 0.00300 = C(61) TO C(31) 
VIBR .0, 0.00300 = C(51) TO C(31) 
VIBR .0, 0.00300 = C(51) TO C(61) 
VIBR .0, 0.00100 = N(12) TO C(22) 
VIBR .0, 0.00100 = C(54) TO C(34) 
VIBR .0, 0.00100 = C(22) TO C(12) 
VIBR .0, 0.00100 = C(22) TO C(33) 
VIBR .0, 0.00300 = C(12) TO N(12) 
VIBR .0, 0.00300 = C(33) TO N(12) 
VIBR .0, 0.00300 = C(33) TO C(12) 
VIBR .0, 0.00100 = C(12) TO O(12) 
VIBR .0, 0.00100 = C(12) TO O(22) 
VIBR .0, 0.00300 = O(12) TO C(22) 
VIBR .0, 0.00300 = O(22) TO C(22) 
VIBR .0, 0.00300 = O(22) TO O(12) 
VIBR .0, 0.00100 = C(43) TO C(53) 
VIBR .0, 0.00100 = C(43) TO C(63) 
VIBR .0, 0.00100 = C(43) TO C(33) 
VIBR .0, 0.00300 = C(63) TO C(53) 
VIBR .0, 0.00300 = C(33) TO C(53) 
VIBR .0, 0.00300 = C(33) TO C(63) 
VIBR .0, 0.00300 = C(43) TO C(22) 
VIBR .0, 0.00100 = C(44) TO C(34) 
VIBR .0, 0.00300 = C(54) TO C(44) 
VIBR .0, 0.00300 = C(22) TO C(44) 
VIBR .0, 0.00300 = C(22) TO C(54) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = O(11) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO O(21) 
U(IJ) .0, 0.02000 = C(11) TO C(21) 
U(IJ) .0, 0.04000 = C(21) TO N(11) 
U(IJ) .0, 0.02000 = C(21) TO C(31) 
U(IJ) .0, 0.02000 = C(31) TO C(41) 
U(IJ) .0, 0.04000 = C(41) TO C(61) 
U(IJ) .0, 0.04000 = C(41) TO C(51) 
U(IJ) .0, 0.04000 = N(12) TO C(22) 
U(IJ) .0, 0.04000 = C(54) TO C(34) 
U(IJ) .0, 0.02000 = C(22) TO C(12) 
U(IJ) .0, 0.02000 = C(22) TO C(33) 
U(IJ) .0, 0.04000 = C(12) TO O(12) 
U(IJ) .0, 0.04000 = C(12) TO O(22) 
U(IJ) .0, 0.04000 = C(43) TO C(53) 
U(IJ) .0, 0.04000 = C(43) TO C(63) 
U(IJ) .0, 0.02000 = C(43) TO C(33) 
U(IJ) .0, 0.04000 = C(44) TO C(34) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
END